Evidence map›Paper›PMID 32092204›Full record

ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020

Synthesis of Fulvene Vinyl Ethers by Gold Catalysis.

Alexander Ahrens, Julia Schwarz, Danilo M Lustosa, Raheleh Pourkaveh, Marvin Hoffmann, Frank Rominger, Matthias Rudolph, Andreas Dreuw, A Stephen K Hashmi

Open access · hybridAbstract read
In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing papers in PubMed
1.4field-weighted citation impact, top 22% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

4 citing papers in PubMed, 26 citations in OpenAlex.

  1. Article
  2. Ligand-controlled divergent asymmetric C(spNature communications · 2025
    Article
  3. Article
  4. Synthesis of Fulvene Vinyl Ethers by Gold Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020
    Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

9 authors at 2 institutions in 3 countries.

Alexander AhrensOrganisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Julia SchwarzOrganisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Danilo M LustosaOrganisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Raheleh PourkavehOrganisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Marvin HoffmannInterdisciplinary Center for Scientific Computing (IWR), Heidelberg University, Im Neuenheimer Feld 205A, 69120, Heidelberg, Germany.
Frank RomingerOrganisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Matthias RudolphOrganisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Andreas DreuwInterdisciplinary Center for Scientific Computing (IWR), Heidelberg University, Im Neuenheimer Feld 205A, 69120, Heidelberg, Germany.
A Stephen K HashmiOrganisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.ORCID http://orcid.org/0000-0002-6720-8602
Heidelberg University · DESharif University of Technology · IR

Funding

Brazilian Council for Scientific and Technological Development (CNPQ)
6 · The paper itself

Abstract

Gold-catalyzed cyclization of 1,5-diynes with ketones as reagents and solvent provides diversely substituted vinyl ethers under mild conditions. The regioselectivity of such gold-catalyzed cyclizations is usually controlled by the scaffold of the diyne. Herein, we report the first solvent-controlled switching of regioselectivity from a 6-endo-dig- to 5-endo-dig-cyclization in these transformations, providing fulvene derivatives. With respect to the functional-group tolerance, aryl fluorides, chlorides, bromides, and ethers are tolerated. Furthermore, the mechanism and selectivity are put to scrutiny by experimental studies and a thermodynamic analysis of the product. Additionally, 6-(vinyloxy)fulvenes are a hitherto unknown class of compounds. Their reactivity is briefly evaluated, to give insights into their potential applications.

Indexed as

aryl cationsfulvene ethersgold catalysisvinyl cationsvinyl ethers

Identifiers

PMID32092204
PMCPMC7216831
OpenAlexW3007023991

What OpenQuestion holds

Textmetadata
LicenceCC BY-NC-ND
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.